Celebrating the Power of 20! – 20 Truths I’ve Learned from 20 Years as an Entrepreneur

#1: Starting a business is not for the faint of heart.  It is risky and stressful. Especially when you leave the security of a big company with benefits, a staff, a reliable paycheck, and guaranteed vacation time to spend with those three little kids you have at home!

#2: You have to be comfortable with unpredictability. You must be able to live with and navigate the world of uncertainty. You’ll wonder where your next paycheck is coming from, whether you’ll have a project next month, and whether today’s clients will be with you tomorrow. It’s helpful to have a spouse or partner that can “fund your unpredictability” at least for a reasonable period of startup time.

In my family, we agreed if the business wasn’t pulling in a certain amount within the first year, I’d give it up and go back to the corporate world. For me, that was the only way I could be comfortable in my decision to break out – knowing that there was an exit strategy in place.

#3: The concept of “balance” is a tricky one to navigate! Entrepreneurs find it difficult to draw a line in the sand between work and personal commitments and respect it. There are no set “work hours” or “workdays”, and you NEVER get a “real” vacation.The laptop has come with me on trips to Italy, England, the Caribbean, and every vacation I’ve taken in the past 20 years. I’ve found “getting it on the calendar” is a mandate for me to make sure I’m there when I need to be for both sides of the line.

#4: Don’t be afraid to ask – and pay for – help from professionals with expertise you need but don’t have.  At first, it is difficult to part with the idea that you can figure it out on your own. But any time you’re spending “figuring it out” is time you are taking away from developing and growing your business – from doing what you do best. Ultimately, this means your business is suffering.

#5: Measure business success over the long haul. Your business is not defined by one good or bad year.  Entrepreneurial success will ebb and flow.There are years of staggering success and years you wonder what the heck happened? You can only try to understand them and learn from them. And then move on to the next year. The key is not to lose confidence or faith in your abilities but continue to pursue your strengths!

#6: Keeping relevant is crucial to keeping up and staying top of mind.  This is true for everything in life, of course, but for most businesses, it’s about technology, understanding upcoming generational attitudes and behaviors, social media leaps and limitations, learning new skills, and expanding your unique capabilities.

#7: Learn to ride the technology wave.  Artificial Intelligence – machines that think, talk, recognize our voices or eyeballs, make recommendations based on our past behavior, and even sometimes trick us into thinking they want to be our friends! – has easily incorporated into our everyday life. Get used to it. If you don’t understand it, learn about it. And importantly, understand how to use it to grow your particular business.

#8: Even if you think it’s too late to start something – START SOMETHING! Make the leap, write the book (or maybe just write the article or blog!), take the class, start the conversation, put yourself out there. The time will pass whether you start something or not.

#9: Spend your time working in your own truth – your unique strengths and talents – the skills, passion and desires that catapulted you into the entrepreneurial life.  It sounds incredibly simplistic, but it can sometimes be difficult to focus on doing what you do best if you’re too worried about others around you doing what they do best!  If you are true to yourself, your beliefs, and your truths, it will be a sacrifice worth suffering. And it will ultimately pay off in the long run with peace of mind.

#10: Protect your business investments – colleagues, client relationships, intellectual property and business trademarks. In areas you’ve spent time and money developing and cultivating, when presented with outside threats and challenges, you simply must protect what you’ve built.  If you’re experiencing an infringement, it means one thing: your trademark or intellectual property is considered valuable by someone else. All the more reason to protect it. Over the years, we’ve been challenged both domestically and internationally several times by others attempting to use one or more of our valuable trademarks, and each time we’ve used legal resources (see #4 above) to stop it. If investments aren’t protected, they become miss leveraged:  increasingly vulnerable and increasingly weakened.

#11: Relationships are everything.  Identify the most important ones and continually nurture them. True in life.  True in family.  True in business. Without being in quality relationships with people, there is no trust, refer-ability, or future. You must invest time and energy into building relationships. That said, there are probably only a handful of relationships you can sustain in each aspect of your life – family, friends, business, community, religion. Feed those relationships and treasure them.

#12: Networking is a skill and a talent.  Networking can be the difference between success and mediocrity; between becoming a new business statistic or a success. It requires a lot of time.  For some people it comes effortlessly, and they execute it genuinely. For me, I can’t stop myself from thinking of it as “selling” or “shilling,” neither of which are big strengths of mine, so 20 years has not been enough for me to perfect this talent. However, my very astute daughter observed that the relationships I have built have been the result of successful networking – no matter how I want to think about the definition of the word!! So, there’s that!

#13: Working with family members or close friends can be rewarding, frustrating, and pleasantly surprising. There’s a degree of confidence that comes from knowing your friends and family have your back. But there’s also a need to separate personal and professional relationships in order to preserve both. Be sure boundaries are conveyed and that each person has his/her own responsibilities.  Encourage everyone involved to work independently in their own truths so that everyone feels productive and fulfilled. And since these people know you better than no other, they often see and point out characteristics in you that (good or bad) you might miss in your own self-observation.

#14: Writing a book is a great way to share your experiences. It allows you to provide useful information, tools, and advice, and you can gain credibility as a thought leader and an expert in your field. Write about what you know well, what you have practiced diligently and for which you can provide many supportive examples. And then ask credible, knowledgeable topic experts who know you well and have experience working with you to read the book and write reviews and an introduction.

I am forever grateful to those clients and colleagues who have provided help, support, and guidance over the years

#15: Ask and be willing to receive.  Feedback is incredibly important as you build your business and brand.  It may not always be pretty or well presented, but it will always be beneficial to help you grow.  Plus, the truths and insights gained can help you come up with new ideas, introduce a new product or positioning, resuscitate a brand without life, or give ideas for how to communicate effectively.

#16: Let loose your inner anthropologist! In the business of consumer/marketing research, getting into someone’s home (or shopping with them in the store or driving with them through the drive-thru) is the BEST way to learn about why they do what they do in life.  It is in the seen, but unsaid; the said combined with in-the-moment behavior, the glimpse into the connections people hold dear and what makes them do what they do that we can begin to understand brand connections and the stories consumers hold dear.

#17: Give back when you can. What you get is WAY more than what you give. For me it was serving on the board of my undergrad’s (DePaul University) Marketing Council, putting on free workshops to college students and lecturing in class, speaking at several industry conferences, and mentoring young people coming into the business.

#18: Keep in mind what drove you. Even in times of great challenge and frustration, recall the drive, passion, and fire that triggered your change. Even after 20 (now, almost 21) years, when I get frustrated or down, I remember the great excitement and anticipation, the freedom and control that helped me take that leap. It mostly serves to re-invigorate and re-energize.

#19: For me the rewards of freedom, flexibility, and independence that entrepreneurship ultimately affords have been completely worth the risk and the stress, no matter the inevitable downsides or hardships. Having been on my own for 20 years, I could not imagine going back to “corporate.”  I suppose one actually can, but after 20 years, who would want to?

#20: Twenty is the new 10! Twenty years go by in a moment– for me, it literally feels like 10 years! Keep goals year by year. Write them down. Without keeping track, sometimes your personal world can become obfuscated by the demands of the entrepreneurial world. Next thing you know, 10 years turns into 20 and while you may be feeling a lot smarter and wiser, you’re also feeling “holy #$*& – how can this possibly be?!